US4667036A - Concentration of light over a particular area, and novel perylene-3,4,9,10-tetracarboxylic acid diimides - Google Patents
Concentration of light over a particular area, and novel perylene-3,4,9,10-tetracarboxylic acid diimides Download PDFInfo
- Publication number
- US4667036A US4667036A US06/642,209 US64220984A US4667036A US 4667036 A US4667036 A US 4667036A US 64220984 A US64220984 A US 64220984A US 4667036 A US4667036 A US 4667036A
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- United States
- Prior art keywords
- alkyl
- formula
- substituted
- tetracarboxylic acid
- cycloalkyl
- Prior art date
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- Expired - Lifetime
Links
- PONZBUKBFVIXOD-UHFFFAOYSA-N 9,10-dicarbamoylperylene-3,4-dicarboxylic acid Chemical class C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=N)C2=C1C3=CC=C2C(=N)O PONZBUKBFVIXOD-UHFFFAOYSA-N 0.000 title claims description 7
- -1 cyano, hydroxyl Chemical group 0.000 claims abstract description 77
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 4
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 9
- 239000004033 plastic Substances 0.000 abstract description 8
- 229920003023 plastic Polymers 0.000 abstract description 8
- 239000002985 plastic film Substances 0.000 abstract description 6
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract description 6
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 abstract description 5
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 abstract 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 13
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 238000005660 chlorination reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000001257 hydrogen Chemical group 0.000 description 2
- 229910052739 hydrogen Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- RPQOZSKWYNULKS-UHFFFAOYSA-N 1,2-dicarbamoylperylene-3,4-dicarboxylic acid Chemical class C1=C(C(O)=O)C2=C(C(O)=O)C(C(=N)O)=C(C(O)=N)C(C=3C4=C5C=CC=C4C=CC=3)=C2C5=C1 RPQOZSKWYNULKS-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 1
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 101100177155 Arabidopsis thaliana HAC1 gene Proteins 0.000 description 1
- SNQBXKUMELPLLH-UHFFFAOYSA-N C(CCC)C1=C(C=2C3=CC=C(C=4C(=CC=C(C5=CC=C(C(=C1C(O)=N)C52)C(O)=N)C43)C(=O)O)C(=O)O)CCCC Chemical compound C(CCC)C1=C(C=2C3=CC=C(C=4C(=CC=C(C5=CC=C(C(=C1C(O)=N)C52)C(O)=N)C43)C(=O)O)C(=O)O)CCCC SNQBXKUMELPLLH-UHFFFAOYSA-N 0.000 description 1
- JZVPCXYFFQVHSZ-UHFFFAOYSA-N C1=CC(C=2C(C(O)=NCCCCCCCC)=C(C(O)=O)C(C(O)=O)=C3C=2C2=CC=C3C(O)=O)=C3C2=CC=CC3=C1 Chemical compound C1=CC(C=2C(C(O)=NCCCCCCCC)=C(C(O)=O)C(C(O)=O)=C3C=2C2=CC=C3C(O)=O)=C3C2=CC=CC3=C1 JZVPCXYFFQVHSZ-UHFFFAOYSA-N 0.000 description 1
- UXOABCSWTQUWSB-UHFFFAOYSA-N ClC=1C(=C(C2=C(C(=C(C=3C4=CC=C(C=5C(=CC=C(C1C23)C54)C(=O)O)C(=O)O)Cl)Cl)C(O)=N)C(O)=N)Cl Chemical class ClC=1C(=C(C2=C(C(=C(C=3C4=CC=C(C=5C(=CC=C(C1C23)C54)C(=O)O)C(=O)O)Cl)Cl)C(O)=N)C(O)=N)Cl UXOABCSWTQUWSB-UHFFFAOYSA-N 0.000 description 1
- VWSCQGLXLJXHTB-UHFFFAOYSA-N OCCN=C(O)C=1C=CC=2C3=CC=C(C=4C(=CC=C(C5=CC=C(C1C52)C(O)=NCCCCCCCC)C43)C(=O)O)C(=O)O Chemical compound OCCN=C(O)C=1C=CC=2C3=CC=C(C=4C(=CC=C(C5=CC=C(C1C52)C(O)=NCCCCCCCC)C43)C(=O)O)C(=O)O VWSCQGLXLJXHTB-UHFFFAOYSA-N 0.000 description 1
- 101100434170 Oryza sativa subsp. japonica ACR2.1 gene Proteins 0.000 description 1
- 101100434171 Oryza sativa subsp. japonica ACR2.2 gene Proteins 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
- H10F77/00—Constructional details of devices covered by this subclass
- H10F77/40—Optical elements or arrangements
- H10F77/496—Luminescent members, e.g. fluorescent sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
Definitions
- the present invention relates to a method of concentrating light by means of fluorescent compounds in plastic sheets or films, and novel perylene-3,4,9,10-tetracarboxylic acid diimides.
- German Laid Open Applications DOS No. 3,001,857, DOS No. 2,620,115 and DOS No. 2,554,226 disclose apparatuses in which visible light in a plastic sheet can be concentrated over a small area by means of incorporated fluorescent centers.
- the compounds required as fluorescent centers in these apparatuses must be very lightfast, so that the apparatus has a sufficiently long life for the particular application, ie. the compounds used as fluorescent centers must have high lightfastness in the plastics used.
- chlorinated bisimides of perylene-3,4,9,10-tetracarboxylic acid meet the above requirements to a large extent
- the conventional chlorinated perylene tetracarboxylic acid diimides prepared by chlorination with elemental chlorine in nitrobenzene or chlorosulfonic acid are obtained in very impure form.
- the chlorination products have to be purified by expensive operations, for example extraction, chromatography or crystallization, these measures, as a rule, having to be repeated a number of times.
- a combination of a number of the stated measures may have to be employed.
- Another disadvantage is that, particularly where chlorination is carried out with elemental chlorine in sulfuric acid, large amounts of highly chlorinated perylimides are formed which, as a rule, are only weakly fluorescent.
- C 5 -C 18 -cycloalkyl which is unsubstituted or substituted by 1 to 5 C 1 -C 4 -alkyl radicals, by 1 or 2 carbo-C 1 -C 4 -alkoxy radicals or by 1 or 2 trifluoromethyl radicals, and the C 5 -C 18 - or C 6 -C 18 -cycloalkyl radicals can contain 1 to 6 rings, the perylimide (I) being obtained by chlorination of a chlorine-free diimide with sulfuryl chloride in an inert solvent in the presence of iodine and/or iodobenzene.
- the chlorinated perylenetetracarboxylic acid diimides used according to the invention give very lightfast colorations which convert the incident light to fluorescent light with high efficiency.
- the wavelength of the fluorescent light is from 500 to 600 nm.
- the perylimides I used according to the invention have the advantage that in most cases a simple purification operation is sufficient to obtain them in very high purity and, for example, free from weakly fluorescent, highly chlorinated, unstable compounds.
- perylimides possessing sensitive groups which impart high solubility in polymers can be converted to defined chlorine compounds, the chlorine atoms entering the perylene system.
- the process gives compounds which are substituted in the perylene radical by chlorine and which exhibit a well defined substitution pattern.
- the tetrachloroperylene-3,4,9,10-tetracarboxylic acid diimides (formula I, wher n is 4) are of the formula ##STR3##
- Suitable unsubstituted or substituted alkyl or cycloalkyl radicals R and R 1 are:
- C 5 -C 18 -cycloalkyl which is unsubstituted or substituted by 1 to 5 C 1 -C 4 -alkyl radicals, by 1 or 2 carbo-C 1 -C 4 -alkoxy radicals or by 1 or 2 trifluoromethyl radicals, and the C 5 -C 18 - or C 6 -C 18 -cycloalkyl radicals can contain 1 to 6 rings.
- preferred perylimides of the formula I are those in which R and R 1 independently of one another are each
- C 4 -C 18 -alkyl n-butyl, n-pentyl, neopentyl, n-hexyl, 2,3-dimethylbutyl, n-heptyl, 3-methylhexyl, 5-methylhex-2-yl, n-octyl, oct-2-yl, 2-ethylhexyl, n-nonyl, dec-1-yl, dec-2-yl, 8-methylnon-2-yl, 2,8-dimethyl-oct-2-yl, undec-1-yl, dodec-1-yl, tridec-1-yl, tetradec-1-yl, hexadec-1-yl and octadec-1-yl,
- radicals R and R 1 from amongst those stated above are C 4 -C 18 -alkyl, in particular the radicals stated under (1a), and 3-(2'-ethylhexyloxy)-prop-1-yl, 6-(2'-ethylhexanonyloxy)-6-methylhept-2-yl, 2,6- and 3,5-dimethylcyclohexyl, 2,6-diisopropylcyclohexyl, 4-methylcyclohexyl, 2,4,6-trimethylcyclohexyl, norbornyl and tricyclo[5,2,1,0]decyl, and n is 3 or 4, in particular 4.
- diimides of the formula II are those in which R and R 1 have the above meanings.
- R and R 1 are linear C 4 -C 13 -alkyl, 4-methylcyclohexyl or norbornyl.
- the present invention furthermore relates to novel perylene-3,4,9,10-tetracarboxylic acid diimides of the formula ##STR4## where R 2 and R 3 are each 3-(2'-ethylhexyloxy)-propyl, 2-ethylhexyl, butyl, octyl, tridecyl, octadecyl, pinan-3-ylmethyl, 6-(2'-ethylhexyanoyloxy)-6-methylhept-2-yl, 4-methylcyclohexyl, 3,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 2,6-diisopropylcyclohexyl or norbornyl, or R 2 is C 4 -C 12 -alkyl, C 1 -C 4 -alkyl-substituted cyclohexyl, or cyclohexyl-C 1 -C 2 -al
- the perylimides of the formula I which are used according to the invention are prepared by chlorinating the corresponding perylimides (I) in which n is 0 with sulfuryl chloride in an inert organic solvent at from 35° to 95° C., preferably from 40° to 85° C., in the presence of a catalyst.
- Suitable catalysts are iodine and iodobenzene, in particular a mixture of these.
- Suitable inert organic liquids for the chlorination are chloroform, trichlorobenzene and, in particular, nitrobenzene.
- the product is precipitated from the reaction mixture by adding a liquid which is miscible with the inert liquid but in which the product is insoluble, and the latter is isolated in a conventional manner.
- the products are obtained in very pure form, give fluorescent yellow colorations in polymers, and can also be used as intermediates for the preparation of other fluorescent dyes.
- the products are, as a rule, purified further and, if required, separated into the individual components, for example by fractional precipitation from concentrated sulfuric acid, by recrystallization from readily removable, high boiling solvents or by boiling up with solvents under milling conditions. Purification can also be carried out by a chromatographic method under atmospheric or superatmospheric pressure.
- perylimide isomers for example those of the formula III, can be obtained even by, for example, simple chromatographic separation methods. These isomers give extremely brilliant colorations and exhibit improved separation of the absorption and emission bands. Furthermore, even the perylimides (II) possessing small radicals R surprisingly are highly soluble in the media used.
- the compounds (I) are incorporated into plastics (media) suitable for the particular application.
- the plastic in the form of granules, is powdered with the required amount of (I), and the granules are then extruded to give sheet-like structures.
- sheet-like structures colored with (I) by dipping the sheet-like structure into a solution of (I), (I) diffusing into the plastic.
- Another possible method comprises polymerizing the (I)-containing monomers or monomer mixtures to give a plastic.
- plastics (media) which can be used for concentrating light for solar cells are polymethyl methacrylate, polymethyl acrylate, polystyrene, polydiethyleneglycol diallyl biscarbonate and other suitable nylons and polycarbonates.
- Chlorinated perylimides of the formula (I) are prepared as described in Example 1.
- R and R 1 and the number of chlorine atoms (n) are given in columns 2 and 3, respectively, of the Table below.
- the amount of sulfuryl chloride used for the preparation is shown in column 4.
- the products are purified by crystallization from a suitable organic solvent, eg. a chlorobenzene, an alkylbenzene, a halomethane, glacial acetic acid, dimethylformamide or a cycloalkane, or by chromatography over silica gel under superatmospheric pressure.
- a suitable organic solvent eg. a chlorobenzene, an alkylbenzene, a halomethane, glacial acetic acid, dimethylformamide or a cycloalkane
- N-hydroxyethyl-N'-octyldiimide used in (a) is obtained by reacting N-octylperylenetetracarboxylic acid monoimide with ethanolamine.
- the monoimide is prepared from perylenetetracarboxylic acid and n-octylamine using the method described in EP-A 39 482.
- Perylimides of the formula ##STR18## are prepared by a method similar to that described in Example 26.
- R 2 and R 3 have the meanings shown in the Table below, and X is chlorine or hydrogen.
- the number of chlorine atoms (n) is shown in column 4 of the Table below, and the remaining radicals X are each hydrogen.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3330916 | 1983-08-27 | ||
| DE3330916 | 1983-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4667036A true US4667036A (en) | 1987-05-19 |
Family
ID=6207575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/642,209 Expired - Lifetime US4667036A (en) | 1983-08-27 | 1984-08-20 | Concentration of light over a particular area, and novel perylene-3,4,9,10-tetracarboxylic acid diimides |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4667036A (enrdf_load_stackoverflow) |
| JP (1) | JPS6089485A (enrdf_load_stackoverflow) |
| DE (1) | DE3434059C2 (enrdf_load_stackoverflow) |
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Also Published As
| Publication number | Publication date |
|---|---|
| JPH0583553B2 (enrdf_load_stackoverflow) | 1993-11-26 |
| DE3434059A1 (de) | 1985-03-14 |
| JPS6089485A (ja) | 1985-05-20 |
| DE3434059C2 (de) | 1997-08-07 |
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